Australian research has demonstrated that students with a disability are more likely to remain out of the full‐time workforce. These research findings have been the catalyst for a call for a comprehensive career development and transition planning approach for all students with disabilities in schools as well as for employers to rethink the role of people with disabilities in the workforce. In the Australian context the transition from school for individuals with a disability is complicated by a disparate and fragmented group of service agencies providing a range of services, including employment, supported accommodation, recreation and leisure pursuits, as well as training and placement, along with, at times, a deep‐seated prejudice towards people with disabilities in the market place. This paper reviews a number of issues and challenges confronting individuals with a disability making the transition from school to the post‐school environment.